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What Is The Functional Group Of An Aldehyde And Ketone?

L9 Functional Groups Alcohol, Phenols, Ethers, Aldehydes, Ketones, Carboxylic Acids

L9 Functional Groups Alcohol, Phenols, Ethers, Aldehydes, Ketones, Carboxylic Acids

Sort Hydrocarbon Derivatives Hydrocarbon derivatives are: • Organic compounds that in addition to C & H atoms also contain atoms of other elements (O, S, N, P, F, Cl, Br) as part of their functional group - A functional group contains atoms other than just carbon and hydrogen • But will still contain some carbon and hydrogen • Functional Groups Discussed Include: - Alcohols & Phenols - Ethers - Thiols - Aldehydes & Ketones - Carboxylic Acids ALCOHOLS- Functional group: Hydroxyl group - OH • General formula: R - OH • IUPAC Name: ALKANOL - An alcohol contains a hydroxyl group (-OH) attached to a carbon chain. • Naming compounds: Replace -ane with -anol at the end of the name - E.g. methane becomes methanol Classification of Alcohols • Primary Alcohol 10 - An alcohol where the C atom bearing the -OH is bonded only to 1 other C atom • Secondary Alcohol 20 - An alcohol where the C atom bearing -OH is bonded to 2 other C atoms • Tertiary Alcohol 30 - An alcohol where the C atom bearing -OH is bonded to 3 other C atoms PHENOLS- Polyphenols present in red wine and are antioxidants which help prevent a range of diseases. • Aromatic Alcohols - -OH group is attached to a benzene ring • Phenol = is the simplest phenol - A phenol contains a hydroxyl group (-OH) attached to a benzene ring - Other phenols contain same basic structure as Phenol with additional substituted groups Phenols Phenols are weak acids - Donate H+, from their -OH group (becomes O-) - Phenols function differently to alcohols • An alcohols can either function as an acid or a base - Phenols are skin & mucous membrane irritants • Contact dermatitis, severe burns - Phenols are Toxic to the liver • Ingestion can be fatal Uses of Phenols Strong anti-septics - Some phenols are used as: • Ho Continue reading >>

Aldehydes And Ketones

Aldehydes And Ketones

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1. Nomenclature Of Aldehydes And Ketones

1. Nomenclature Of Aldehydes And Ketones

Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone. The IUPAC system of nomenclature assigns a characteristic suffix to these classes, al to aldehydes and one to ketones. For example, H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at the end of a carbon chain, it is by default position #1, and therefore defines the numbering direction. A ketone carbonyl function may be located anywhere within a chain or ring, and its position is given by a locator number. Chain numbering normally starts from the end nearest the carbonyl group. In cyclic ketones the carbonyl group is assigned position #1, and this number is not cited in the name, unless more than one carbonyl group is present. If you are uncertain about the IUPAC rules for nomenclature you should review them now. Examples of IUPAC names are provided (in blue) in the following diagram. Common names are in red, and derived names in black. In common names carbon atoms near the carbonyl group are often designated by Greek letters. The atom adjacent to the function is alpha, the next removed is beta and so on. Since ketones have two sets of neighboring atoms, one set is labeled α, β etc., and the other α', β' etc. Very simple ketones, such as propanone and phenylethanone (first two examples in the right column), do not require a locator number, since there is only one possible site for a ketone carbonyl function. Likewise, locator numbers are omitted for the simple dialdehyde at t Continue reading >>

Polarity Of Organic Compounds

Polarity Of Organic Compounds

Polarity of Organic Compounds Principles of Polarity: The greater the electronegativity difference between atoms in a bond, the more polar the bond. Partial negative charges are found on the most electronegative atoms, the others are partially positive. In general, the presence of an oxygen is more polar than a nitrogen because oxygen is more electronegative than nitrogen. The combination of carbons and hydrogens as in hydrocarbons or in the hydrocarbon portion of a molecule with a functional group is always NON-POLAR. Summary of Polarity See below for the details. Polarity Ranking of the Functional Groups: (most polar first) Amide > Acid > Alcohol > Ketone ~ Aldehyde > Amine > Ester > Ether > Alkane An abbreviated list to know well is: Amide > Acid > Alcohol > Amine > Ether > Alkane Organic Functional Group Polarity and Electrostatic Potential: The molecular electrostatic potential is the potential energy of a proton at a particular location near a molecule. Negative electrostatic potential corresponds to: partial negative charges (colored in shades of red). Positive electrostatic potential corresponds to: partial positive charges (colored in shades of blue). Boiling Point Definition: In a liquid the molecules are packed closely together with many random movements possible as molecules slip past each other. As a liquid is heated, the temperature is increased. As the temperature increases, the kinetic energy increases which causes increasing molecular motion (vibrations and molecules slipping pas each other). Eventually the molecular motion becomes so intense that the forces of attraction between the molecules is disrupted to to the extent the molecules break free of the liquid and become a gas. At the temperature of the boiling point, the liquid turns into a gas. The m Continue reading >>

Protecting Groups In Grignard Reactions

Protecting Groups In Grignard Reactions

Now that we’ve gone over the most useful reactions of Grignard reagents – addition to epoxides, aldehydes, ketones, and esters – let’s go back to the topic of how to make Grignard reagents, albeit with a twist. Here’s the summary for today’s post: Introducing Yet Another Way To Royally Screw Up Making A Grignard Reagent In a previous post we said that there are cases where making Grignard reagents can fail due to the presence of an acidic proton. Like this example. The problem here is that Grignard reagents are strong bases, and will react with even weak acids (like alcohols). If we try to make a Grignard on a molecule with an acidic functional group, we’ll end up destroying our Grignard instead. We saw that one way around this problem was to protect alcohols as some kind of inert functional group (like an ether) which doesn’t react with our Grignard. Similarly, there are other cases of molecules where making a Grignard reagent will fail for similar reasons. For example: why does this reaction not give the desired Grignard reagent? The problem here, as you might have guessed if you read the last post, is that this Grignard reagent reacts with itself!!! Once formed, the Grignard would react with the ketone from the starting material. This could then react with Mg to give a new Grignard, which would react with more ketone… and so on. The result is a mess. “Protecting Groups” Mask A Functional Group From Attack If we were able to find some way to “mask” the ketone in this case, possibly as some unreactive functional group that is completely inert to Grignard reagents, then we could then make the Grignard reagent without causing any problems of self-reactivity. Then, once we’re done, we could then “unmask” the protecting or masking group, rev Continue reading >>

Ketone

Ketone

Not to be confused with ketone bodies. Ketone group Acetone In chemistry, a ketone (alkanone) /ˈkiːtoʊn/ is an organic compound with the structure RC(=O)R', where R and R' can be a variety of carbon-containing substituents. Ketones and aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered "simple" because they do not have reactive groups like −OH or −Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing −COOH.[1] Many ketones are known and many are of great importance in industry and in biology. Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallest ketone. Nomenclature and etymology[edit] The word ketone is derived from Aketon, an old German word for acetone.[2][3] According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -ane of the parent alkane to -anone. The position of the carbonyl group is usually denoted by a number. For the most important ketones, however, traditional nonsystematic names are still generally used, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names,[4] although some introductory chemistry textbooks use systematic names such as "2-propanone" or "propan-2-one" for the simplest ketone (CH3−CO−CH3) instead of "acetone". The common names of ketones are obtained by writing separately the names of the two alkyl groups attached to the carbonyl group, followed by "ketone" as a separate word. The names of the alkyl groups are written alphabetically. When the two alkyl groups are the same, the prefix di- is added before the name of alkyl group. The positions of other groups are indicated by Greek letters, the α-carbon being th Continue reading >>

Reactions Of Aldehydes And Ketones

Reactions Of Aldehydes And Ketones

Reference: McMurry Ch 9 George et al Ch 2.6 Structure and bonding Contain a carbonyl group, C=O Aldehydes have at least one H attached to the carbonyl group, ketones have two carbon groups attached to the carbonyl group Carbon of the carbonyl group is sp2 hybridised The C=O bond is polar Aldehydes and ketones strongly absorb radiation around ~ 1700 cm-1 in the infrared region Nomenclature Aldehydes The longest chain containing the CHO group gives the stem; ending �al If substituents are present, start the numbering from the aldehyde group - C1 Ketones The longest chain containing the carbonyl group gives the stem; ending �one If substituents are present number from the end of the chain so the carbonyl group has the lowest possible number There are non-systematic names for the common aldehydes and ketones With the exception of oxidation of aldehydes, the reactions of aldehydes and ketones is dominated by nucleophilic addition. 1. Oxidation of aldehydes Aldehydes (but not ketones) may be oxidised to carboxylic acids with Cr2O72- / H+ Example: 2. Nucleophilic addition The double bond of the carbonyl group undergoes an addition reaction The polarity of the C=O bond results in the addition of a nucleophile (Nu-) to the carbon atom, breaking of the double bond and addition of H+ to the oxygen is always the second step and results in an alcohol Common nucleophiles include the Grignard reagent (RMgX), hydride ion (H- from LiAlH4 or NaBH4) In summary Examples: Grignard reaction Recap � generation of a Grignard reagent from an alkyl halide and magnesium in dry diethyl ether solvent Grignard reagents also react with carbon dioxide to generate carboxylic acids after addition of aqueous H+ Reduction Reduction of the non-polar C=C or C� C bonds in alkenes and alkynes respecti Continue reading >>

Naming Aldehydes

Naming Aldehydes

Aldehydes are organic chemical compounds that include a -carbonyl group (i.e. an oxygen atom attached to a carbon atom by a double covalent bond) and a hydogen atom attached to the carbon atom of the carbonyl group: That is, aldehydes are a class or category of organic chemical compounds that include a carbon atom attached to both an oxygen atom (by a double covalent bond), and also a hydrogen atom (by a single covalent bond). Bearing in mind that carbon atoms form a total 4 single covalent bonds - or equivalent in combinations of double or triple bonds, a carbon atom attached to both an oxygen atom (by a double covalent bond) and a hydrogen atom (by a single covalent bond) can only form one other single covalent bond linking it to the rest of an organic molecule. It must therefore always be the first- or last - (which are equivalent positions) carbon atom in the chain of carbon atoms that form the organic molecule of which it is a part. This position of the -carbonyl group attached to the end- carbon in a carbon-chain is important because it distinguishes aldehydes from a similar category of organic compounds, called ketones. Aldehyde molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms. Continue reading >>

Chapter 10 Introduction To Organic Chemistry: Alkanes

Chapter 10 Introduction To Organic Chemistry: Alkanes

Functional Groups Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Elements in Organic Compounds In organic molecules, carbon atoms bond with four bonds. mostly with H and other C atoms. sometimes to O, N, S, sometimes to halogens F, Cl, and Br. Functional Groups Functional groups are a characteristic feature of organic molecules that behave in a predictable way. composed of an atom or group of atoms. groups that replace a hydrogen atom in the corresponding alkane. a way to classify families of organic compounds. Alkenes and Alkynes Alkenes contain a double bond between adjacent carbon atoms. Alkynes contain a triple bond. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Alcohols and Ethers An alcohol contains the hydroxyl (-OH) functional group. In an ether, an oxygen atom is bonded to two carbon atoms. –C–O–C– . R’–O–R or R–O–R R=alkyl group and R’=different alkyl group Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Aldehydes and Ketones An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Carboxylic Acids and Esters Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O ║ — C—OH An ester contains the carboxyl group between carbon atoms. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Amines and Amides In amines, the functional group is a nitrogen atom. | —N — In amides, the hydroxyl Continue reading >>

The Structure And Naming Of Aldehydes & Ketones

The Structure And Naming Of Aldehydes & Ketones

Doc Brown's GCE A Level AS A2 Chemistry Revising Advanced Level Organic Chemistry Revision Notes Part 5 CARBONYL COMPOUNDS NOMENCLATURE of ALDEHYDES and KETONES 5.1 The molecular structure and naming of ALDEHYDES and KETONES - including nomenclature of some isomers Nomenclature of aldehydes & ketones names and structures of aldehydes & ketones How to name aldehydes? How to name ketones? Nomenclature of substituted aldehydes or ketones - examples of acceptable names, displayed formula of aldehydes and ketones, graphic formula of aldehydes and ketones, molecular formula of aldehydes and ketones, skeletal formula of aldehydes and ketones, structural formula of aldehydes and ketones and homologous series of aldehydes and ketones, how to name the carbonyl group of compounds known as aldehydes and ketones Organic Chemistry Part 5 sub-index: 5.1.1 Nomenclature introduction * 5.1.2 Examples of aldehydes 5.1.3 Examples of ketones * 5.1.4 Other examples of substituted ketones 5.1.5 Oxidation sequence: alcohol ==> aldehyde/ketone ==> carboxylic acid Revision notes on the structure and naming-nomenclature of Aldehydes and Ketones 5.1.1 Introduction to Aldehyde and Ketone Nomenclature How do you name aldehydes? How do you name ketones? How do you name substituted aldehydes or ketones? Aldehydes and ketones are a group of compounds containing the carbonyl group, C=O. Aldehydes always have a hydrogen atom attached to the carbon of the carbonyl group, so the functional group is -CHO (see diagram above). The functional group is shown by using 'al' in the suffix part of the name e.g. methanal, ethanal, propanal etc. The prefix for the aldehyde name is based on the parent alkane minus the e. No number is required for the aldehyde group because the aldehyde group cannot be anything else ex Continue reading >>

Aldehyde

Aldehyde

Aldehyde, any of a class of organic compounds, in which a carbon atom shares a double bond with an oxygen atom, a single bond with a hydrogen atom, and a single bond with another atom or group of atoms (designated R in general chemical formulas and structure diagrams). The double bond between carbon and oxygen is characteristic of all aldehydes and is known as the carbonyl group. Many aldehydes have pleasant odours, and in principle, they are derived from alcohols by dehydrogenation (removal of hydrogen), from which process came the name aldehyde. Aldehydes undergo a wide variety of chemical reactions, including polymerization. Their combination with other types of molecules produces the so-called aldehyde condensation polymers, which have been used in plastics such as Bakelite and in the laminate tabletop material Formica. Aldehydes are also useful as solvents and perfume ingredients and as intermediates in the production of dyes and pharmaceuticals. Certain aldehydes are involved in physiological processes. Examples are retinal (vitamin A aldehyde), important in human vision, and pyridoxal phosphate, one of the forms of vitamin B6. Glucose and other so-called reducing sugars are aldehydes, as are several natural and synthetic hormones. Structure of aldehydes In formaldehyde, the simplest aldehyde, the carbonyl group is bonded to two hydrogen atoms. In all other aldehydes, the carbonyl group is bonded to one hydrogen and one carbon group. In condensed structural formulas, the carbonyl group of an aldehyde is commonly represented as −CHO. Using this convention, the formula of formaldehyde is HCHO and that of acetaldehyde is CH3CHO. The carbon atoms bonded to the carbonyl group of an aldehyde may be part of saturated or unsaturated alkyl groups, or they may be alicycli Continue reading >>

Aldehydes And Ketones

Aldehydes And Ketones

Nomenclature: Aldehydes: functional group suffix = -al (review) Ketones: functional group suffix = -one (review) Functional group prefix = oxo- (Note that an aldehyde is higher priority than a ketone) window0._cover(false)Jmol._Canvas2D (Jmol) "window0"[x] window1._cover(false)Jmol._Canvas2D (Jmol) "window1"[x] window2._cover(false)Jmol._Canvas2D (Jmol) "window2"[x] window3._cover(false)Jmol._Canvas2D (Jmol) "window3"[x] methanal ethanal propanone 5-oxohexanal Physical Properties: The polar nature of the C=O (due to the electronegativity difference of the atoms) means dipole-dipole interactions will occur. Though C=O can not hydrogen-bond to each other, the C=O can accept hydrogen bonds from hydrogen bond donors (e.g. water, alcohols). The implications of these effects are: higher melting and boiling points compared to analogous alkanes lower boiling points than analogous alcohols more soluble than alkanes but less soluble than alcohols in aqueous media Structure: The carbonyl group consists of an O atom bonded to a C atom via a double bond, C=O, via an sp2 hybridisation model similar to that of ethene, H2C=CH2 (review ?) with bond angles close to 120o. O is connected to the carbonyl C via a σ and a π bond. The C=O and the two other atoms attached to the C are co-planar. This implies that the two lone pairs on O are in sp2 hybrid orbitals. window4._cover(false)Jmol._Canvas2D (Jmol) "window4"[x] window5._cover(false)Jmol._Canvas2D (Jmol) "window5"[x] window6._cover(false)Jmol._Canvas2D (Jmol) "window6"[x]loading... -- required by ClazzNode methanal ethene propanone Reactivity: Therefore the general mode of reaction of aldehydes and ketones is attack of a nucleophile at the electrophilic carbonyl C: You can look at the accessiblity effect in the following series of alde Continue reading >>

Nomenclature Of Aldehydes & Ketones

Nomenclature Of Aldehydes & Ketones

Aldehydes and ketones contain the carbonyl group. Aldehydes are considered the most important functional group. They are often called the formyl or methanoyl group. Aldehydes derive their name from the dehydration of alcohols. Aldehydes contain the carbonyl group bonded to at least one hydrogen atom. Ketones contain the carbonyl group bonded to two carbon atoms. Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen, alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone. Naming Aldehydes The IUPAC system of nomenclature assigns a characteristic suffix -al to aldehydes. For example, H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at the end of a carbon chain, it is always is given the #1 location position in numbering and it is not necessary to include it in the name. There are several simple carbonyl containing compounds which have common names which are retained by IUPAC. Also, there is a common method for naming aldehydes and ketones. For aldehydes common parent chain names, similar to those used for carboxylic acids, are used and the suffix –aldehyde is added to the end. In common names of aldehydes, carbon atoms near the carbonyl group are often designated by Greek letters. The atom adjacent to the carbonyl function is alpha, the next removed is beta and so on. If the aldehyde moiety (-CHO) is attached to a ring the suffix –carbaldehyde is added to the name of the ring. The carbon attached to this moiety will get the #1 location number in naming the ring. Aldehydes take their name Continue reading >>

What Is Ketone? - Definition, Structure, Formation & Formula

What Is Ketone? - Definition, Structure, Formation & Formula

Background of Ketone Did you know that our friend aldehyde has a very close relative named ketone? By definition, a ketone is an organic compound that contains a carbonyl functional group. So you may be wondering if aldehydes and ketones are relatives, what makes them different? Well, I am glad you asked because all you have to remember is this little guy: hydrogen. While aldehyde contains a hydrogen atom connected to its carbonyl group, ketone does not have a hydrogen atom attached. There are a few ways to know you are encountering a ketone. The first is by looking at the ending of the chemical word. If the suffix ending of the chemical name is '-one,' then you can be sure there is a ketone present in that compound. Want to know another way to tell if a ketone is lurking around the corner? By its physical property. Ketones have high boiling points and love water (high water solubility). Let's dig a little deeper with the physical property of a ketone. The oxygen in a ketone absolutely loves to take all the electrons it can get its hands on. But, by being an electron-hogger, oxygen's refusal to share creates a sticky situation where some atoms on the ketone have more or less charge than others. In chemistry, an electron-hogging atom is referred to as being electronegative. An electronegative atom is more attractive to other compounds. This attractiveness, called polarity, is what contributes to ketones' physical properties. Structure & Formula Ketones have a very distinct look to them; you can't miss it if you see them. As shown in Diagram 1, there are two R groups attached to the carbonyl group (C=O). Those R groups can be any type of compound that contains a carbon molecule. An example of how the R group determines ketone type is illustrated in this diagram here. The Continue reading >>

Chapter 16: Aldehydes And Ketones (carbonyl Compounds)

Chapter 16: Aldehydes And Ketones (carbonyl Compounds)

The Carbonyl Double Bond Both the carbon and oxygen atoms are hybridized sp2, so the system is planar. The three oxygen sp2 AO’s are involved as follows: The two unshared electorn pairs of oxygen occupy two of these AO’s, and the third is involved in sigma bond formation to the carbonyl carbon. The three sp2 AO’s on the carbonyl carbon are involved as follows: One of them is involved in sigma bonding to one of the oxygen sp2 AO’s, and the other two are involved in bonding to the R substituents. The 2pz AO’s on oxygen and the carbonyl carbon are involved in pi overlap, forming a pi bond. The pi BMO, formed by positive overlap of the 2p orbitals, has a larger concentration of electron density on oxygen than carbon, because the electrons in this orbital are drawn to the more electronegative atom, where they are more highly stabilized. This result is reversed in the vacant antibonding MO. As a consequence of the distribution in the BMO, the pi bond (as is the case also with the sigma bond) is highly polar, with the negative end of the dipole on oxygen and the positive end on carbon. We will see that this polarity, which is absent in a carbon-carbon pi bond, has the effect of strongly stabilizing the C=O moiety. Resonance Treatment of the Carbonyl Pi Bond 1.Note that the ionic structure (the one on the right side) has one less covalent bond, but this latter is replaced with an ionic bond (electrostatic bond). 2.This structure is a relatively “good” one, therefore, and contributes extensively to the resonance hybrid, making this bond much more thermodynamically stable than the C=C pi bond, for which the corresponding ionic structure is much less favorable (negative charge is less stable on carbon than on oxygen). 3.The carbonyl carbon therefore has extensive car Continue reading >>

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